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Method for separation and purification of 2-adamantanecarboxylic acid and 1-adamantanecarboxylic acid

A technology of adamantanecarboxylic acid and a purification method is applied in the field of separation and purification of adamantanecarboxylic acid mixtures, and can solve problems such as difficulty in separation, difficulty in separation of mixtures, environmental pollution and the like

Inactive Publication Date: 2011-11-23
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the two have the same molecular weight, functional group and parent ring, the properties between the two are close, and the separation of the mixture is difficult, especially the separation of the mixture (recrystallization residue, etc.) with close content is more difficult and pollutes the environment.

Method used

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  • Method for separation and purification of 2-adamantanecarboxylic acid and 1-adamantanecarboxylic acid
  • Method for separation and purification of 2-adamantanecarboxylic acid and 1-adamantanecarboxylic acid
  • Method for separation and purification of 2-adamantanecarboxylic acid and 1-adamantanecarboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Add 2g of 1-adamantanecarboxylic acid and 2-adamantanecarboxylic acid mixture raw material (about 50:50) into a 50mL round bottom flask, add 10mL of methanol, add 0.2g of 98% sulfuric acid as a catalyst, heat up to 65°C with magnetic stirring carry out esterification reaction. After reacting for 15 minutes, the reaction system was sampled, 1 mL of water was added, extracted with 1 mL of ethyl acetate and injected into GC for analysis, the reaction results were as follows: figure 1 . where t R 7.972 is methyl 1-adamantanecarboxylate, t R 8.235 is methyl 2-adamantanecarboxylate, t R 10.431 is 1-adamantanecarboxylic acid, t R 10.872 is 2-adamantanecarboxylic acid. 33.5% of methyl 1-adamantanecarboxylate, 3.3% of methyl 2-adamantanecarboxylate, 16.9% of 1-adamantanecarboxylate, 41.3% of 2-adamantanecarboxylate. Stop the reaction for separation, add 20 mL of water, add 10% NaOH solution to alkaline (PH ≥ 10), separate the aqueous solution from the ester, acidify the aq...

Embodiment 2

[0014] Add 2g of 1-adamantanecarboxylic acid and 2-adamantanecarboxylic acid mixture raw material (about 50:50) into a 50mL round bottom flask, add 10mL of methanol, add 0.2g of 98% sulfuric acid as a catalyst, heat up to 65°C with magnetic stirring carry out esterification reaction. After 30 minutes, it was detected that methyl 1-adamantanecarboxylate was 44.2%, methyl 2-adamantanecarboxylate was 4.3%, and 1-adamantanecarboxylate was 6.8%. 2-Adamantanecarboxylic acid 40.1%. Stop methylation reaction, adopt embodiment 1 identical aftertreatment, water layer obtains 0.6g of 2-adamantanecarboxylic acid, product fusing point 140-142 ℃, GC analysis content reaches 98.0%, as figure 2 . That 1 H NMR (400MH Z CDCl 3 )δ1.63-1.67(m 2H)δ1.68-1.78(m4H)δ1.86-1.93(m 6H)δ2.35(s 2H)δ2.67(s 1H)δ12.4(s 1H); 13 C NMR (100MH Z CDCl 3 ) 27.36 27.37 29.37 33.54 37.31 38.06 49.44 181.21. 0.8 g of 1-adamantanemethanol was obtained from the ester layer, and the content of GC analysis reach...

Embodiment 3

[0016] Add 2g of 1-adamantanecarboxylic acid and 2-adamantanecarboxylic acid mixture raw material (about 50:50) into a 50mL round bottom flask, add 10mL of methanol, dropwise add 0.8g of 98% sulfuric acid as a catalyst, and heat up to 65°C. Stir to carry out the esterification reaction. After reacting for 15 minutes, GC analysis showed that methyl 1-adamantanecarboxylate was 51.6%, methyl 2-adamantanecarboxylate was 41.2%, and 2-adamantanecarboxylate was 6.3%. 1-Adamantanecarboxylic acid 0.8%. After reacting for 30 minutes, methyl 1-adamantanecarboxylate was 52.3%, methyl 2-adamantanecarboxylate was 43.0%, and 2-adamantanecarboxylate was 4.5%. 1-Adamantanecarboxylic acid 0.3%. Less than 0.1 g of 2-adamantanecarboxylic acid was isolated. It shows that the amount of sulfuric acid catalyst is increased, and the rate of methylation is accelerated. If the reaction speed is too fast, it will be difficult to control the end point of the reaction. If the methyl esterification rea...

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Abstract

The invention relates to a method for separation and purification of an adamantanecarboxylic acid mixture, especially a method for separation and purification of 2-adamantanecarboxylic acid and 1-adamantanecarboxylic acid. Comprising the steps of esterification and separation, the method is characterized in that: in the esterification reaction, 98% sulfuric acid is employed as a catalyst, with the ratio of the catalyst to raw materials in a range of from 0.5-3:10, the reaction time is 15-140min, and the reaction temperature ranges from 55-70DEG C; then water and NaOH are added to make the pH value of the solution above 10, so that a water and an ester layer is separated. In the invention, the separation of 1-adamantanecarboxylic acid and 2-adamantanecarboxylic acid is realized through an esterification reaction, i.e. through the esterification differences between 2-adamantanecarboxylic acid and 1-adamantanecarboxylic acid. Therefore, not only is the method of the invention simple and practicable, but also the product generated after separation and purification has satisfying purity. Especially, residues from adamantanecarboxylic acid production can be fully utilized, so that the discharge of "three wastes" can be reduced and environmental pollution is prevented. With remarkable economic benefit and social benefit, the method of the invention is economical and environmental friendly.

Description

technical field [0001] The invention relates to a method for separating and purifying an adamantanecarboxylic acid mixture, in particular to a method for separating and purifying 2-adamantanecarboxylic acid and 1-adamantanecarboxylic acid. Background technique [0002] Adamantane is a positively symmetrical and very stable cage-like hydrocarbon, which is widely used in medicine, functional polymers, surfactants, lubricants, photographic photosensitive materials, aviation and so on. [0003] 1-adamantanecarboxylic acid is generally synthesized by adamantane and its derivatives through Koch-haaf reaction, 1-adamantanecarboxylic acid is the main raw material for the synthesis of rimantadine hydrochloride (rimantadine); 1-adamantanecarboxylic acid methyl ester is synthesized after reduction Adamantane Methanol (ZL200610052600.8) can be used in the production of photoresist, etc. [0004] 2-Adamantanecarboxylic acid also has a good application prospect in medicine and photosensi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C61/135C07C51/493
Inventor 胡晓春孔黎春
Owner ZHEJIANG NORMAL UNIVERSITY
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